Metal Free Bi (hetero) aryl Synthesis: A Benzyne Truce–Smiles Rearrangement

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Abstract: A new benzyne transformation is described that affords versatile biaryl structures without recourse to transition‐metal catalysis or stoichiometric amounts of organometallic building blocks. Aryl sulfonamides add to benzyne upon fluoride activation, and then undergo an aryl Truce–Smiles rearrangement to afford biaryls with sulfur dioxide extrusion. The reaction proceeds under simple reaction conditions and has excellent scope for the synthesis of sterically hindered atropisomeric biaryl amines.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Metal Free Bi (hetero) aryl Synthesis: A Benzyne Truce–Smiles Rearrangement ; volume:55 ; number:7 ; year:2016 ; pages:2450-2453 ; extent:4
Angewandte Chemie / International edition. International edition ; 55, Heft 7 (2016), 2450-2453 (gesamt 4)

Creator: Holden, Catherine M.
Sohel, Shariar M. A.
Greaney, Michael F.

DOI: 10.1002/anie.201510236

URN: urn:nbn:de:101:1-2022101406192669949686

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:32 AM CEST

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Associated

Holden, Catherine M.
Sohel, Shariar M. A.
Greaney, Michael F.

Other Objects (12)

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SYNTHESIS OF 3-BROMO-1-METHYLPHENOTHIAZINES BY SMILES REARRANGEMENT

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Metal Free Bi (hetero) aryl Synthesis: A Benzyne Truce–Smiles Rearrangement

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SYNTHESIS OF 7-PHENOXYPHENOTHIAZINES BY SMILES REARRANGEMENT

SYNTHESIS OF 3-BROMO-1-METHYLPHENOTHIAZINES BY SMILES REARRANGEMENT

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SYNTHESIS OF 3-BROMO-1-METHYLPHENOTHIAZINES BY SMILES REARRANGEMENT

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Metal Free Bi (hetero) aryl Synthesis: A Benzyne Truce–Smiles Rearrangement

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SYNTHESIS OF FLUOROPHENOTHIAZINES BY SMILES REARRANGEMENT

SYNTHESIS OF FLUOROPHENOTHIAZINES BY SMILES REARRANGEMENT

SYNTHESIS OF PHENOTHIAZINES VIA SMILES REARRANGEMENT

SYNTHESIS OF PHENOTHIAZINES VIA SMILES REARRANGEMENT

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SYNTHESIS OF 7-PHENOXYPHENOTHIAZINES BY SMILES REARRANGEMENT

SYNTHESIS OF 3-BROMO-1-METHYLPHENOTHIAZINES BY SMILES REARRANGEMENT

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SYNTHESIS OF 3-BROMO-1-METHYLPHENOTHIAZINES BY SMILES REARRANGEMENT

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SYNTHESIS OF SUBSTITUTED 3-CHLORO-l-METHYLPHENOTHIAZINES VIA SMILES REARRANGEMENT

Photochemical (Hetero-)Arylation of Aryl Sulfonium Salts

Photochemical (Hetero-)Arylation of Aryl Sulfonium Salts

Asymmetric, Remote C (sp 3)−H Arylation via Sulfinyl‐Smiles Rearrangement

Asymmetric, Remote C (sp 3)−H Arylation via Sulfinyl‐Smiles Rearrangement

SYNTHESIS OF 6-CHLORO-9-METHYL-N-METHOXYPHENOTHIAZINES VIA SMILES REARRANGEMENT

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